2019 - Keon Johnson '20 named TSSAA Div. II Mr. Basketball for the second consecutive year in March
2019 - Webb Family Reunion hosted on campus in June to help kick off 150th Anniversary
2019 - 150th Anniversary Celebration began in August with first day of class and student, faculty and staff drone photo in 150 configuration
2019 - First TSSAA 11-man football game at Lagler Field
2019 - 150th Anniversary & Friends Socials began in September
2019 - Follin/Webb 150 Series began in October with presentations by Andrew Maraniss, Wayne White and Thompson Webb III
2019 - Coast-to-Coast Toasts were hosted in various U.S. and international locations on Sawney Webb's birthday Nov. 11
2019 - It was announced on Dec. 11 that Ken Cheeseman would join Webb as new head of school in July 2020
2020 - Follin/Webb 150 Series continued in January with a presentation by Dr. John McCardell
2020 - In response to the COVID-19 Pandemic, decision made to close campus and utilize Distance Learning for the remainder of the 2019-2020 school year
2020 - 8th Grade Graduation and Middle School Book Awards Ceremony held on campus July 10 following the Governor's directives
2020 - Class of 2020 graduation was held on campus July 11 following the Governor's directives